2-(2-碘-5-甲氧基苯基)-N,N-二甲基乙酰胺 | 99540-20-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(2-碘-5-甲氧基苯基)-N,N-二甲基乙酰胺
• 英文名称: 2-iodo-5-methoxy-N,N-dimethylbenzeneacetamide
• 英文别名: (6-iodo-3-methoxy)phenyl-N,N-dimethylacetamide；N,N-dimethyl-2-iodo-5-methoxybenzeneacetamide；2-(2-Iodo-5-methoxyphenyl)-N,N-dimethylacetamide
• CAS: 99540-20-2
• 化学式: C₁₁H₁₄INO₂
• 分子量: 319.142
• InChiKey: MCNOFYYFRXRROA-UHFFFAOYSA-N

物化性质

• 熔点：
  86-89 °C
• 沸点：
  390.9±37.0 °C(Predicted)
• 密度：
  1.551±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、乙酸乙酯、乙醚、

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  2-(2-碘-5-甲氧基苯基)-N,N-二甲基乙酰胺 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以76%的产率得到2-iodo-5-methoxy-N,N-dimethylbenzeneethanamine
  参考文献：
  名称：

  2-Ethynylbenzenealkanamines. A new class of calcium entry blockers

  摘要：

  A series of 2-(aryl- or alkylethynyl)benzenealkanamines were synthesized. They exhibit antihypertensive activity in spontaneously hypertensive rats and coronary vasodilator activity with minimal negative inotropic activity in the "Langendorff" guinea pig heart in vitro. They have been shown to exert their activity by inhibition of Ca2+ influx across cell membranes. Optimal activity is found among the N-(arylethyl)-5-methoxy-alpha-methyl-2-(phenylethynyl)ben zeneethanamines and -propanamines.

  DOI：

  10.1021/jm00398a023
• 作为产物：
  描述：

  2-(2-碘-5-甲氧基苯基)乙酸 在 草酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 2-(2-碘-5-甲氧基苯基)-N,N-二甲基乙酰胺
  参考文献：
  名称：

  2-Ethynylbenzenealkanamines. A new class of calcium entry blockers

  摘要：

  A series of 2-(aryl- or alkylethynyl)benzenealkanamines were synthesized. They exhibit antihypertensive activity in spontaneously hypertensive rats and coronary vasodilator activity with minimal negative inotropic activity in the "Langendorff" guinea pig heart in vitro. They have been shown to exert their activity by inhibition of Ca2+ influx across cell membranes. Optimal activity is found among the N-(arylethyl)-5-methoxy-alpha-methyl-2-(phenylethynyl)ben zeneethanamines and -propanamines.

  DOI：

  10.1021/jm00398a023

文献信息

• Acetylene amines and their use as vasodilators and antihypertensives
  申请人：McNeilab, Inc.

  公开号：US04725602A1

  公开（公告）日：1988-02-16

  Acetylenes of the following formula (I): ##STR1## wherein Y, m, R.sup.1, R.sup.2, R.sup.3, n and R.sup.4 are defined herein and R.sup.5 is hydrogen, alkyl, cycloalkyl or substituted alkyl are useful vasodilators and antihypertensives.

  以下式(I)的乙炔化合物：##STR1## 其中Y、m、R.sup.1、R.sup.2、R.sup.3、n和R.sup.4的定义见下文，R.sup.5是氢、烷基、环烷基或取代烷基，是有用的血管扩张剂和降压药物。
• Syntheses and Characterization of the Acyl Glucuronide and Hydroxy Metabolites of Diclofenac
  作者：Jane R. Kenny、James L. Maggs、Xiaoli Meng、Deborah Sinnott、Stephen E. Clarke、B. Kevin Park、Andrew V. Stachulski

  DOI：10.1021/jm030891w

  日期：2004.5.1

  quantities of 2-4 are required and their syntheses and characterization are described here. Key steps were a convenient two-step preparation of aniline 5 from phenol, efficient and selective 6-iodination of amide 18, and high-yielding Ullmann couplings to generate diarylamines 11 and 21. The acyl glucuronide 4 was obtained by Mitsunobu reaction of 1 (free acid) with allyl glucuronate 23 followed by Pd(0) deprotection

  在人类中，常用的非甾体类抗炎药双氯芬酸1的代谢主要产生4'-羟基2、5-羟基3和酰基葡糖醛酸4代谢物。所有这三种代谢物都与这种广泛使用的药物相关的罕见特发性不良反应有关。因此，对于1的机械毒理学研究，需要大量的2-4，并在此描述其合成和表征。关键步骤包括从苯酚方便地分两步制备苯胺5，酰胺18进行高效且选择性的6碘化以及高产率的Ullmann偶联以生成二芳基胺11和21.酰基的葡糖醛酸苷4通过1的Mitsunobu反应获得葡萄糖醛酸23烯丙基酯，然后使用Pd（0）脱保护，使用公开程序的修改方法。我们报告了4的全部特征，并注意到该重要的代谢物已首次以纯净和大量提供。我们还报告了合成代谢产物的代谢命运：2和3在大鼠中是葡萄糖醛酸化的，但在体内和通过醌亚胺中间体的酶促合成中，只有3个形成了谷胱甘肽加合物。通过酶促合成获得先前未描述的3的谷胱甘肽加合物。如氰基硼氢化钠捕获所示，化合物4形成了亚胺连接
• Methods for the treatment of hypertension
  申请人：McNeilab, Inc.

  公开号：US04898889A1

  公开（公告）日：1990-02-06

  Acetylene compounds of the formula (I): ##STR1## wherein Y, R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are as described herein, m is 0-3, n is 0-2 and Ar is phenyl or an aromatic heterocycle are disclosed. The compounds possess antihypertensive and anti-anginal properties and may be used in the treatment of humans. Methods for the preparation and use of such acetylene compounds are also disclosed.

  公开了化学式（I）的乙炔化合物：##STR1##其中Y、R.sub.1、R.sub.2、R.sub.3和R.sub.4如本文所述，m为0-3，n为0-2，Ar为苯或芳香杂环。这些化合物具有降压和抗心绞痛的特性，可用于人类的治疗。还公开了制备和使用这种乙炔化合物的方法。
• Methods for the treatment of angina
  申请人：McNeilab, Inc.

  公开号：US04960798A1

  公开（公告）日：1990-10-02

  Acetylene compounds of the formula (I): ##STR1## wherein Y, R.sub.1, R.sub.2 R.sub.3, and R.sub.4 are as described herein, m is 0-3, n is 0-2 and Ar is phenyl or an aromatic heterocycle are disclosed. The compounds possess anti-hypertensive and anti-anginal properties and may be used in the treatment of humans. Methods for the preparation and use of such acetylene compounds are also disclosed.

  公开了式子（I）的乙炔化合物：##STR1## 其中Y，R.sub.1，R.sub.2，R.sub.3和R.sub.4如此描述，m为0-3，n为0-2，Ar为苯基或芳香杂环。这些化合物具有抗高血压和抗心绞痛特性，可用于人类的治疗。还公开了制备和使用这种乙炔化合物的方法。
• Acetylene derivatives for the treatment of hypertension and angina
  申请人：McNeilab, Inc.

  公开号：EP0145361A2

  公开（公告）日：1985-06-19

  57 Acetylene compounds of the formula (I): wherein Y, R1, R,, R3, and R4 are as described herein, m is 0-3, n is 0-2 and Ar is pehnyl or an aromatic heterocycle are disclosed. The compounds possess antihypertensive and anti-anginal properties and may be used in the treatment of humans. Methods for the preparation and use of such acetylene compounds are also disclosed.

  57 本发明公开了式 (I) 的乙炔化合物：其中 Y、R1、R、R3 和 R4 如本文所述，m 为 0-3，n 为 0-2，Ar 为正烷基或芳香杂环。 这些化合物具有抗高血压和抗心绞痛的特性，可用于人类治疗。 本发明还公开了制备和使用此类乙炔化合物的方法。